Interview Only: ESPN Legal Analyst Ryan Smith discusses the witnesses at the Diddy.

Summary

The Stephen A. Smith Show – Episode Summary Release Date: May 24, 2025

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Introduction

In this episode of The Stephen A. Smith Show, host Stephen A. Smith delves into two major topics: the high-profile trial of Sean "Diddy" Combs and a controversial action taken by the Trump administration against Harvard University. Joined by ESPN Legal Analyst Ryan Smith, the discussion provides deep insights into both legal battles, examining testimonies, legal strategies, and potential outcomes.

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I. The Sean "Diddy" Combs Trial

A. Overview of the Trial

Stephen A. Smith opens the discussion by summarizing the current state of Sean "Diddy" Combs' trial, where Combs faces five federal charges, including sex trafficking and racketeering. The trial has spanned two full weeks of testimony, bringing forth various testimonies that paint a troubling picture of Combs' alleged criminal activities.

B. Key Testimonies and Evidence Presented

1. David James – Former Personal Assistant ([01:16] - [02:58])

   • Testimony Highlights:
     • David James disclosed that he advised Cassie Ventura, Combs' former girlfriend, to "get out" of her situation.
     • Ryan Smith: “[...] she couldn't because Combs controlled so much of her life.” ([01:50])

2. Regina Ventura – Mother of Cassie Ventura ([02:58] - [04:26])

   • Testimony Highlights:
     • Regina expressed fear for her daughter's safety and documented the physical abuse Cassie endured.
     • She reiterated Cassie’s lack of autonomy due to Combs' pervasive control.
     • Ryan Smith: “[...] the prosecution's offering,” a methodical assembly of testimonies to build the case. ([03:30])

3. Kid Cudi – Musician and Actor ([05:00] - [07:15])

   • Testimony Highlights:
     • Kid Cudi recounted a brief relationship with Cassie Ventura and alleged that Combs, driven by rage and jealousy, orchestrated the firebombing of his sports car.
     • This testimony underscores the violent tendencies attributed to Combs.
     • Kid Cudi's Claim: “[...] Combs broke into my home and coordinated the firebombing of my high-end sports car.” ([06:00])

C. Legal Analysis by Ryan Smith

Ryan Smith provides a comprehensive analysis of the prosecution's case against Combs:

• Building the Case: He likens the trial to assembling a broad puzzle, where each testimony and piece of evidence contributes to the overarching narrative of a criminal enterprise.

  “It's a very broad puzzle that's being put together...” ([03:30])

• Racketeering and Sex Trafficking: Smith explains how various testimonies support the claims of racketeering by showing Combs' control over multiple individuals and activities across different states, thereby fitting the federal racketeering (RICO) framework.

  “You have Cassie talking about what happened to her, other people talking about what they experienced...” ([04:26])

• Coercion and Control: Emphasizing the coercive environment Cassie was allegedly subjected to, Smith highlights how this undermines the notion of consent, a core element in the sex trafficking charges.

  “The coercion was so strong... it was almost as if she wasn't able to get out.” ([05:00])

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II. Jury Perception and Potential Trial Outcomes

A. Damaging Impact of Testimonies

Stephen A. Smith questions the credibility of Regina Ventura's testimony, suggesting potential defense strategies that may portray her as complicit by not intervening sooner.

• Smith's Concern:

  “I don't know how believable the mom comes across when you suddenly say you were so worried...” ([04:26])

B. Prosecution vs. Defense Strategies

Ryan Smith discusses the balance the prosecution must maintain between presenting compelling evidence and ensuring the jury remains focused on the criminal aspects rather than personal animosity towards Combs.

• Key Points:

  • Immunity for Associates: The prosecution leverages testimonies from individuals who received immunity in exchange for their cooperation, thereby strengthening the case against Combs.

    “They've given immunity...” ([08:50])

  • Potential Video Evidence: The possibility of introducing video evidence of the "freak offs" could be a double-edged sword. While it may reinforce the prosecution's narrative, the defense is likely to challenge its admissibility due to prejudicial impacts.

    “If you see Diddy in a video... that's going to look to the jury like he's orchestrating the entire thing.” ([13:39])

C. Ryan Smith’s Evaluation of Combs’ Standing

Based on the accumulated testimonies and evidence, Ryan Smith assesses that Combs' situation appears increasingly unfavorable.

• Assessment:

  “He looks far worse now. He looks like a person who is completely out of control to this jury.” ([15:29])

• Jury’s Dilemma: Smith contemplates the jurors’ potential biases, questioning whether accusations of personal misconduct might overshadow the specific charges of sex trafficking and racketeering.

  “If the jury comes back and says, we think your behind needs to go to jail... what can you do?” ([17:05])

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III. Transition to Harvard University Controversy

Midway through the episode, Stephen A. Smith shifts the focus to a developing story involving Harvard University, following a significant administrative action by the Trump administration.

A. Overview of the Situation

• Government Action: The Department of Homeland Security revoked Harvard's ability to enroll international students, citing an unsafe campus environment due to alleged anti-American and pro-terrorist activities. Accusations also include coordination with the Chinese Communist Party.

• Harvard’s Response: The university has filed a lawsuit claiming the government's actions violate the First Amendment and argue that the measures amount to unconstitutional retaliation.

• Immediate Development: A federal judge temporarily blocked the administration's plan, putting the issuance of the order on hold.

B. Legal Insights from Ryan Smith

Ryan Smith provides his expertise on the implications of this conflict between Harvard and the Trump administration.

• First Amendment Concerns: Smith explains that Harvard is framing the issue as an infringement on its academic freedom and autonomy.

  “The government trying to determine what they teach, who teaches it, and how they do it... violates their First Amendment rights.” ([20:19])

• Government’s Justification: The administration argues that Harvard's actions have fostered an unsafe environment, necessitating federal intervention.

  “You're facilitating on campus anti Semitism... that is why we need to take certain action.” ([20:19])

• Potential Legal Path: Smith anticipates that this dispute will escalate through the judicial system, possibly reaching the Supreme Court.

  “I would not be surprised if this ends up in the Supreme Court...” ([21:54])

• Broader Implications: He warns of the slippery slope where government control over educational institutions could extend beyond current actions, affecting academic freedoms extensively.

  “If you're a university, you have to look at that and say, that cannot happen.” ([21:54])

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Conclusion

This episode of The Stephen A. Smith Show offers a comprehensive look into two significant legal battles: the ongoing trial of Sean "Diddy" Combs and the contentious action against Harvard University by the Trump administration. With expert analysis from Ryan Smith, listeners gain a deeper understanding of the complexities involved, the strategies of both prosecution and defense, and the broader implications these cases hold for justice and academic freedom.

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Notable Quotes

• Ryan Smith on Building the Case Against Combs:

  “It's a very broad puzzle that's being put together...” ([03:30])

• On Coercion in the Sex Trafficking Case:

  “The coercion was so strong... it was almost as if she wasn't able to get out.” ([05:00])

• Regarding Potential Video Evidence:

  “If you see Diddy in a video... that's going to look to the jury like he's orchestrating the entire thing.” ([13:39])

• On Harvard’s Legal Battle:

  “The government trying to determine what they teach, who teaches it, and how they do it... violates their First Amendment rights.” ([20:19])

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This summary encapsulates the key discussions and insights from The Stephen A. Smith Show episode, providing listeners with a clear and detailed overview of the topics covered.

Transcript

[Podcast Host]

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[Ryan]

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[Stephen A. Smith]

Now onto the latest in the Sean Diddy Combs trial where Diddy is facing five five federal charges involving sex trafficking and racketeering. The trial is wrapping up a second full week of testimony. This week we heard testimony from Combs former personal assistant David James, who testified he told Cassie Ventura, Combs former girlfriend, that she needed to, quote, get out, end quote. Ben Ventura claimed she couldn't because Combs controlled so much of her life. On Tuesday we heard testimony from Regina Ventura, the mother of Cassie Ventura, who told jurors that she was quote, scared for my daughter's safety, end quote, and that she documented the physical abuse Cassie suffered at the hands of Combs, who prosecutors claimed coerced the young Aventura and others into participating in drug fueled sex shows. And yesterday jurors heard testimony from musician and actor Kid Cudi. He told the court that he briefly dated Cassie Ventura and he believes the rap mogul, in a fit of rage and jealousy, broke into his home and coordinated the firebombing of his high end sports car. He said the pair dated only briefly, but yet it was marked by violent threats from Combs that prompted him and Ventura to stop seeing one another. Well, we know that's bad. We know that's bad and I got a lot of stuff to say about that, but not at the expense of taking time away from My next guest, who is a legal analyst for abc, obviously a sports center anchor for espn, does an outstanding job for the Disney family. The one and only Ryan Smith, legal analyst extraordinaire, right here with Stephen A. How you doing, Ryan? How's everything?

[Ryan Smith]

Yeah, man, I'm good. How are you doing?

[Stephen A. Smith]

I'm doing all right. So you heard that intro and is there anything there that you believe is ultra damaging to Too Diddy, considering the charge is sex trafficking and racketeering? I mean, we know it doesn't look good for him. Domestic violence and how people feared for their lives. We get that part. But I'm still waiting to hear about sex trafficking and racketeering. Is there anything that you've heard over the last week or so that would indicate such a, such a charge is valid?

[Ryan Smith]

Yeah, absolutely. But I think the way people have to look at it is they have to look at it as a very broad puzzle that's being put together. I think when people look at cases like this, Stephen, they look for that smoking gun. Oh, this is the thing that proves that Diddy ran a criminal enterprise and he had all these people involved to facilitate this criminal activity over a period of years. That's essentially the racketeering part. But you have to put it together methodically. So what you have is Cassie talking about what happened to her, other people talking about what they experienced. You have people coming in, talking about being flown in, doing freak offs in different states. That gives it a federal aspect. And then you have assistants talking about cleaning up, people telling Cassie different things. But she's feeling coerced to stay into relationships. That's part of the sex trafficking case. Sex trafficking case. So all of this, as hard as it might be for people to seem, all of this are pieces of a puzzle that are slowly coming together to prove the case the prosecution's offering.

[Stephen A. Smith]

I'm wondering how damaging her mother's testimony was to Diddy as opposed to herself. Herself. I mean, you're her mother. What do you mean? You, you was worried about your daughter's safety, but still, you know, you allowed the situation to continue for a lengthy period of time, spanning years. I don't know how believable the mom comes across when you suddenly say you were so worried about your daughter's safety. Nevertheless, we don't see. Was there any effort whatsoever to relieve your daughter from being in that situation?

[Ryan Smith]

You know, that's part of the defense's case right there. They're going to make the argument that, hey, she was voluntarily in a relationship and you didn't help get her out. But I like that you use the word allow because that's what the prosecution is really trying to hook onto. They're trying to hook onto the idea that there was no allowing because the tentacles were so deep into Cassie, the coercion was so strong, it was almost as if she wasn't able to get out. Now, I know people are going to hear that and say, look, she had free will. She was in this relationship for so long. There were many things she could have done. Absolutely. But I think part of what people are trying, what the prosecution is trying to show here with sex trafficking is the coercion can be so strong. The elements of bringing somebody in, having them used for a commercial sect act, and then force, using force, coercion, threats, things like that, to keep them in the activity makes it hard for the person to get out. You've heard people talk about how Cassie said, hey, everything I have is tied into this in many ways. I'm paraphrasing. But when you have that kind of situation, the allowing part goes away. And for the prosecution, it's about proving it wasn't about allowing. She could not get out of this thing because of the criminal enterprise that existed.

[Stephen A. Smith]

Well, here's the interesting part too, because David James, the former personal assistant, said that he had told Cassie to get out. Excuse me. But she said she couldn't get out. Why? Because she couldn't. Because Combs controlled so much of her life. So now we get into a tricky portion of it, Ryan. There's bosses. There's always, if you're in a subordinate role, there's always someone who could have some degree of control over your career, but that control is relatively subjective. Like certain situations you walk away from, say, hell, no, I'm not dealing with that. Bye, I'll walk out. I'll walk out. So one could easily argue, what do you mean, control? Because if he wasn't stopping you from walking out the door, if he wasn't stopping you from walking on with your. Walking on with your life, but you just may not have enjoyed the level of success that you're having right now. Yeah, that's not great. But in the same breath, a lot of people in America have to deal with circumstances, not obviously, the sex acts and all of that stuff. But I'm talking about the level of control individual with power may have over somebody's career. What do you say to that?

[Ryan Smith]

Yeah, I say that what you're talking about essentially is consent. You're talking about a situation where people can walk away. And I think that's a great point. But the flip side of that is, is she in a situation? And I'm not making the case for her, but I'm kind of coming from where the prosecution is coming from. It's so deep in some ways. And this is where things come in, like the drugging and the threats and the violence. It's so deep, the coercion and the control that the person feels like there is not a way out of the situation. The despite what assistants are saying, despite what the mother is talking about, people urging her to get out. That's part of the case they're trying to build. And that's how it broadens out to the commercial enter to the criminal, to the RICO enterprise that they're alleging and the sex trafficking. That in many of these cases, people are in a situation, they're being engaged for this sex act. And that the coercion, the threats, all of that, the violence, it's so powerful. Hey, if you. I'm giving an example here. Hey, if you leave, I'm going to do this, I'm going to do that. The drug age. Cassie testified about how the drugging went on for a long period of time, as did the freak offs that she's in this sort of fog and this haze, all of that stuff contributing to the fact that the aspect of control that some of us might feel like we have at, say, at a job where we're being mistreated and we want to leave and we just walk is different from this circumstance here. That's how they're trying to paint it.

[Stephen A. Smith]

So with that being said, I'm looking at Diddy right now and it doesn't look good for him. There's no way around that. However, I find myself asking Ryan, where are the other. Where are the other villains in all of this?

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[Stephen A. Smith]

Because sex trafficking and racketeering, one man, one individual. I don't want to accuse the, you know, the district attorney, a prosecutor, a grandstanding. But most people out here feel like we need to see more than just Diddy, if it's as comprehensive as they're trying to make this all seem. To that you say what?

[Ryan Smith]

Yeah, to that I say they're using assistance and other people, they're giving immunity. So you've heard people talk who have immunity in this case, who've said, hey, I was a part of this. I cleaned up certain things. I tried to get her out of there. I saw some of this stuff go down. And that's where the conspiracy aspect of this, that's where we start seeing as they see it, an enterprise being built, operated by Diddy Diddy associated with it, to try to make these things happen over a period of years. That's where we see the freak off context come in. But you're talking about a different situation. You're talking about the bigger names, the people who might have been involved. They're not approaching that just yet. Is that a part of where they might go? In some ways, possibly. But I think for them, it's easier to get the people who they know were involved based on all the evidence they secured and say, hey, we're gonna offer you immunity if you tell us what happened. And I think for many people, this is gonna be interesting for the jury because the jury is hearing all this. And just remember, when you hear all of this, it's important for the prosecution that the jury not hear Diddy as a bad guy or a weird guy or a guy who does crazy things, but not criminal things. The criminal part comes in when you start bringing in the associates who talk about all the different levels of things that happened. One person testified about carrying a bag of cash. Another person talked about the payoff that was made to the hotel, all these different things to sustain the criminal enterprise. It's those people, those underlings, all those associates that he had with them that they want to get to try to build that enterprise. Not the big names that you might be thinking of.

[Stephen A. Smith]

What about the actual sex itself? And what I mean by that, Ryan, is this. If you were one of those individuals that engaged in the actual sexual activity, you are being somebody that was a participant. But isn't it possible that you may have had nothing to do with the actual sex trafficking and racketeering allegations? You were just a participant engaging in sexual activity?

[Ryan Smith]

That's right. And they had a couple of people, they had some people testify like that. They had a guy testify his nickname is the Punisher, talked about how he was hired to have sex with Cassie. He's not somebody who's part of the enterprise. Who he is is somebody who was engaged to come in and have this sex trafficking activity with Cass. The other reason why you bring in a guy like that is he talked about how freak offs happened in different states. Now you're seeing the federal aspect of this case, which is why it's a federal case and not a state case, which is why you can allege things like rico, which is why some of these charges which involve interstate commerce come into play. Because some of these activities, they're alleging for the prosecution, they're saying Diddy had these things. He controlled this enterprise over multiple states and he brought people in to engage in this sextant, to continue the means of what he wanted to do. This. He used all these. This largesse, he had this power, this influence to create this criminal enterprise using these people.

[Stephen A. Smith]

But where are the other women other than Cassie who are alleged to have been participants in all of this?

[Ryan Smith]

I think they're going to start trying to weave some of those people in because it's not just about Cassie. There are other people I think the prosecution is going to try to bring into this case to say they were involved in this in some way. But Stephen A. For them, Cassie is the star witness. She is everything in this case. You have to believe Cassie and what she went through and believe that she is coerced. Why? Because you have the video, which sticks out more than anything. When you talk about what juries see in a courtroom, you can hear testimony for days that it's harrowing. But when you see a videotape of somebody being abused, that is the one thing that sticks in your mind more than anything. More than that also, it's the fact that she had this long standing relationship with Sean Diddy Combs. So she had a front row seat to the freak offs to everything that happened to everybody else. So she is the main player in all of this. There might be other people weaved in who were subject to this, who did it, coerced in some way, at least according to the prosecution, to try to facilitate this criminal enterprise. But it all comes down to her and how the jury sees her, which is why it's so important for the prosecution that they don't see her as a voluntary consensual partner, but rather someone who was coerced into being in this relationship and could not get out.

[Stephen A. Smith]

Are we going to see any videos of the freak offs? Because I know the media has been asking for access to that. Is that going to happen?

[Ryan Smith]

I think it's going to be debatable. I'm interested. You know, it's one of those issues where I'm just not sure. I know the defense is going to fight it tooth and nail and they have good reason. When you start seeing, as I said earlier, when you see a video that sticks with you more than anything else. So if you see Giddy in a video with a bunch of people having sex for the defense, that's going to look to the jury like he's orchestrating the entire thing. Their whole point is these are Parties, consensual parties. This is not anything more than that. So for them to have that video in the courtroom is extremely damaging. They're going to fight it tooth and nail, and it's all going to come down to the judge. Is it the kind of evidence that's important to the prosecution's case to help prove the case and won't have the prejudicial value of disrupting the defense's case on the other side? The judge will have to decide that. But these videos, if they do come out in that courtroom, extremely damaging for Diddy because his mere presence in the video while people are, and I'm just making. I don't know what's in them, but if people are presumably having sex with him being there, that's incredibly damaging because that's the very orchestration view that the prosecution is trying to get the jury to see.

[Stephen A. Smith]

Last question on this particular subject. And it's not necessarily a legal question. It's just your level of expertise because of what you know about this business, about the law, about the impact on a jury, et cetera, based on your expertise at this moment in time, even without the videos of freak offs being seen, just based strictly on Cassi Ventura's testimony, the. The cross examination she endured, witnesses and participants that came and testified already, including her mother. Not that she was a participant, but, you know, just having a relationship with her daughter. Does Diddy look the same, better or worse than when this trial first started?

[Ryan Smith]

Far worse. Far worse. Because we know all the details now. It's more than just what we might have read in the papers. It's more than just the scuttlebutt that people heard. And now we know the details of what went down from people who actually experienced it. And it's just from the perspective of the kind of person he was, how he treated Cassie, how she tried to get out of it. Kid Cudi talking about the threats. We had heard Kid Cudi talking about Diddy before this trial, but what he said about him being a marvel supervillain, allegations of firebombing his car, far worse. Far worse now. But here's the key. Being a bad guy does not make you a criminal. And so for me, this case is not fully put together yet. It's just beginning. They're just starting to put the puzzle together, but the puzzle is not complete. I think having the threat, say, for example, Kid Cudi shows things like obstruction. We're trying to threaten him to keep people silenced, to say, what's happening in this criminal enterprise. But do we clearly see the enterprise yet? Do we clearly see the sex trafficking yet? Are we clearly, as a jury believing that this is an involuntary relationship and a consenting relationship? I think that remains to be seen. But no matter what, no matter how you come out of this, in no way does he look good. He looks far worse. And he looks like a person who is completely out of control to this jury. I think if I'm sitting in that jury box, the question I have, if I'm a juror, is, is he just an extremely bad person or is he a criminal?

[Stephen A. Smith]

Last question. I apologize. One thing you just said that made me think of this.

[Ryan Smith]

Yeah.

[Stephen A. Smith]

What if they don't know whether or not sex trafficking and racketeering has been proven, but they consider him so despicable and they consider his behavior criminal because of what he was seeing on video doing the Cassie and what have you that they convict him anyway? I mean, if they find him guilty, it's not as if a judge or a defense attorney is going to be able to definitively say, you know what your case, you know, sex trafficking and racketeering was not why you made this decision. You made this decision against him because of his acts of domestic violence. It's not like they're going to be.

[Ryan Smith]

Able to prove that.

[Stephen A. Smith]

If the jury comes back and says, we think your behind needs to go to jail, I mean, what can you do?

[Ryan Smith]

You're making a couple. You're making me think of a couple of things there. The first thing is, I think no matter what happens here, they're going to appeal. So they're going to appeal and they're going to argue that the case wasn't proven. The defense is just going to say they didn't prove the elements of the case, and they're going to try to get information to try to figure out what happened here. But more than that, they're going to say the elements of the case weren't proven. The other thing is, you're talking about, what if a jury looks at this and says, didn't rise to the level of RICO or sex trafficking, but it's something lesser. Sometimes juries get compromised verdicts. They look at the other charges and they say, well, I see the obstruction of justice, or I see elements of the conspiracy charges, the lesser charges, so let's convict them of that stuff and not the bigger stuff that I don't necessarily see, like rico. So that is something the defense also wants to look out for and the prosecution doesn't want to happen. The prosecution wants them to see A full enterprise. They want to get as many years in prison as they can. And when you got an obstruction connection, that's not a lot of time. So the jury has a lot of ways they can go here, which is why it's so important for them to put the puzzle together fully if you're the prosecution. But there is always a risk when you're trying a case like this that a jury doesn't fully see what you're trying to explain. And they either compromise or they end up in a mistrial. Or for the prosecution, worst of all worlds, they say not guilty.

[Stephen A. Smith]

Ryan, before I let you get on out of here, I need to switch subjects and I need your counsel on something here. Thursday, the Trump administration revoked Harvard University's ability to enroll international students in its escalating battle with the Ivy League school, saying thousands of current students must transfer to other schools or leave the United States of America. Just as an aside to our audience before I ask you about this, the Department of Homeland Security says Harvard has created an unsafe campus environment by allowing, quote, anti American pro terrorist agitators, end quote, to assault Jewish students on campus. It also accused Harvard of coordinating with the Chinese Communist Party, saying it hosted and trained members of a Chinese paramilitary group as recently as 2024. This morning, just this morning, Harvard challenged the decision, calling it unconstitutional retaliation for defying the White House's political demands. In a lawsuit filed today in federal court, Harvard said the government's actions violates the First Amendment and will have an immediate and devastating effect for Harvard and more than 7,000 visa holders. And then, hours later, a federal judge temporarily blocked the Trump administration from carrying out its plan. Your thoughts about this situation and how it will ultimately unfold based on your level of expertise, sir?

[Ryan Smith]

Yeah. First of all, Harvard is looking at this like a First Amendment issue. And they're seeing this really as the government trying to come in and determine what they teach, who teaches it, and how they do it. And they're saying that violates their First Amendment rights. The government on the other side is saying, hey, you are facilitating on campus anti Semitism, things of that nature. And that's why we need to take certain action against you. But what this really is is an ongoing fight between these two sides. And from Harvard's perspective, it's the government trying to control how they run their university, which, if you're a university, you have to look at that and say, that cannot happen. That's a slippery slope for us. This day it's this thing. The next day it's the Next thing, the third day, they're controlling exactly how we run our university, and that can't happen. So, so how this plays out, I think right now, as you said, the tro, it's been blocked, the order has been blocked. But this is, I think the government in many cases has done this recently. The government has been testing the limits of the law, testing what they can do to exercise control over what they see at certain campuses, over how they view those campuses should be run. So I see this eventually going to the higher courts, if not the Supreme Court, because this has been sort of the pattern of the government recently. It's been this idea of, hey, if it's not working the way we want it to work, or if, if we see something happening that we think is wrong, then we're going to try to put down a real heavy hammer on them, see if there's pushback, and then let it go to the courts and see how it plays out. I would not be surprised if this ends up in the Supreme Court at the end of the day.

[Stephen A. Smith]

Ryan Smith, legal analyst extraordinaire for ABC Sports center, anchor for ESPN, and a host of other things the brothers gifted. Make no mistake about it. Honored to have him on the show, as always. Enjoy your weekend, my man. We will talk soon. You take care of yourself, all right? Thank you so much.

[Ryan Smith]

You too, man. Take care.

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